What a trip! Makes sense for people--searching/non-searching souls--to go into the Big Apple like gangbusters (am I being rank or crude by still calling it the Big Apple? Sorry, I live in Florida). One night I left Port Authority (long Greyhound layover) and decided to walk up as much of Central Park West as I could. In the late 1970's, sorta scary, but I love my memories of it. Made it up to 110th Street, then dashed back to get my bus. By 1996 I had gotten to all 50 states and about 30 other countries on less than $6K, grand total. Just a real nice lifestyle for anybody to imbibe in, no matter to what extent they acclimate to the local turf.

Matt- there was just a great read in one of the recent New Yorker mags about a journalist(?) who did just this- I can't recall the exact issue but you might enjoy the POV of a guy who did this same thing 40 years ago. Would be cool to trace some of his walks and see what they are like now.

Love this. I once walked from Battery Park up to 125th, I was too broke for a cab, I couldn't find my MetroCard (turns out it was lodged in between pages in my journal), and it was nice day so I figured, why not? In all the times I've visited NYC since, it still remains one of the most memorable experiences I've had in the city.

But some logistical questions--how are you plotting your routes? Are you inviting folks to walk with you? And how long do you think it'll take you to cover the entirety of the five boroughs?

I plot the routes by eyeballing my progress map and trying to quickly (usually right before I walk out the door) come up with something that covers new ground and doesn't leave weird little isolated unwalked stretches that will be hard to get to later. I've just been couchsurfing around, so I don't usually know where I'll be staying too far in advance, which means I have to be flexible with the route planning.

I've had a good number of people walk with me, but it can be tough to coordinate because all my planning is so last-second.

I have at least two more years of walking ahead of me on this project, but I wouldn't be surprised if it ends up taking longer.

Beautifully written. Definitely following you.
If you havent read it yet - or to those reading it interested in Lao Tzu - I highly recommend getting your hands on The Empty Boat. Great beginners guide to Lao Tzu's message.

Great post. Be sure to write down everything you discover along the way, so when you've seen everything and know nothing, you'll be able to look back and re-discover it. This is meant only part in jest. The other part is more discovery of patterns you might not recognize as you're encountering them.
On a seperate note, I had set a similar goal, to run every street in our town as part of training for a marathon. Not only did it give me something to focus on, but it gave me a flavor for all the nooks and crannies I might not have otherwise noticed.

thanks, Matt. I loved this post. Dee Hock, guy who built Visa and wrote the best book I've read in years (One from Many), talks about wisdom being the extend of our knowledge divided by the number of things we know about. his thinking is that as we've modernized, the denominator has grown exponentiall - that we used to know a lot about a little, and know we know a little about a lot, and that that is an equation that isn't great for wisdom. your effort made me want to try and focus and learn and great depth. thanks.